Annapolis was just ranked #5 in Travel CNN’s best American Towns to visit, and for good reason too. Let’s break down what made this charming, quaint little town so special, but first, here is the top 5 towns CNN listed.
- Annapolis, Maryland
- Bend, Oregon
- Asheville, North Carolina
- Missoula, Montana
- Ithaca, New York
Annapolis’ ranking is, in part, because it holds on to its past, refusing to abandon its colonial roots in favor of complete modernity. As we see cities transforming through the use of new technologies, it’s always a pleasant surprise to see a city steeped in its history. As the lore goes, there is even a tavern there that is so old, it was serving Americans before the colonies were even formed (George Washington and Ben Franklin are rumored to have stayed there too!)
Wandering the streets will feel like you’re in a film dated back to the 18th century with its untouched, historical, quaint buildings and cobblestone streets. Walk from souvenir ship to restaurant, purchasing small heirlooms that represent the city and dining on two of the city’s most popular seafoods: oysters and crab.
There is a heavy arts scene that comes through in their seasons, as multiple festivals and events take over the city. This summer we’ll see the Annapolis Crab Feast, Wednesday Night Sailboat Races, and a Dinner Under the Stars Initiative that helps liven up the cobblestone streets and give back to the town’s businesses that have stood there since the 18th century.
Crossing from downtown to Eastport, you can take in the city’s maritime history and port on the Chesapeake Bay over a drink at one of their many restaurants and breweries, like Foreword Brewing.
Don’t forget to see the city the way it’s intended, from out on the water. Water Taxis, sail boats, and The Wilma Lee, owned by the Maritime Museum (another can’t miss landmark) and a piece of history.
Maryland is only 45 minutes from D.C. and serves as the perfect vacation spot for enjoying a weekend at a slower pace.
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